title: Synthesis of 2,4,5-trisubstituted thiazoles via Lawesson's reagent-mediated chemoselective thionation-cyclization of functionalized enamides.
abstract: An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.
authors.affiliation: New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore-560064, Karnataka, India.
authors.forename: S Vijay
authors.initials: SV
authors.lastname: Kumar
authors.forename: G
authors.initials: G
authors.lastname: Parameshwarappa
authors.forename: H
authors.initials: H
authors.lastname: Ila
mesh_terms: D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D013844:Thiazoles